PL80851B1 - - Google Patents
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- Publication number
- PL80851B1 PL80851B1 PL14074470A PL14074470A PL80851B1 PL 80851 B1 PL80851 B1 PL 80851B1 PL 14074470 A PL14074470 A PL 14074470A PL 14074470 A PL14074470 A PL 14074470A PL 80851 B1 PL80851 B1 PL 80851B1
- Authority
- PL
- Poland
- Prior art keywords
- imidazolyl
- acetic acid
- radical
- alkyl
- group
- Prior art date
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 63
- -1 alkyl radicals Chemical class 0.000 claims description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 150000002460 imidazoles Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 150000003254 radicals Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 150000002366 halogen compounds Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- 210000002966 serum Anatomy 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 208000015181 infectious disease Diseases 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 150000004702 methyl esters Chemical class 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- OMLSYNQYPRJYAR-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 OMLSYNQYPRJYAR-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 241000222122 Candida albicans Species 0.000 description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- AVKUPUSZQPSBOD-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-2,2-diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)O)C1=NC=CN1 AVKUPUSZQPSBOD-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 230000000843 anti-fungal effect Effects 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241001480043 Arthrodermataceae Species 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229940095731 candida albicans Drugs 0.000 description 3
- 230000037304 dermatophytes Effects 0.000 description 3
- IQDLKFJCEIJFGN-UHFFFAOYSA-N ethyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCC)C1=NC=CN1 IQDLKFJCEIJFGN-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- BMEHATQTULZMSC-UHFFFAOYSA-N methyl 2,2-bis(4-chlorophenyl)-2-(1h-imidazol-2-yl)acetate Chemical compound C=1C=C(Cl)C=CC=1C(C=1C=CC(Cl)=CC=1)(C(=O)OC)C1=NC=CN1 BMEHATQTULZMSC-UHFFFAOYSA-N 0.000 description 3
- KQPURLPHEFAXQG-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-bis(4-methoxyphenyl)acetate Chemical compound C=1C=C(OC)C=CC=1C(C=1C=CC(OC)=CC=1)(C(=O)OC)C1=NC=CN1 KQPURLPHEFAXQG-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- IZPXHZWRFDQWLT-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1-morpholin-4-yl-2,2-diphenylethanone Chemical compound N=1C=CNC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C(=O)N1CCOCC1 IZPXHZWRFDQWLT-UHFFFAOYSA-N 0.000 description 2
- XEZZSIVYLCTXPO-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N)C1=NC=CN1 XEZZSIVYLCTXPO-UHFFFAOYSA-N 0.000 description 2
- LCDMIMDUWFHYFQ-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-n-methyl-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)NC)C1=NC=CN1 LCDMIMDUWFHYFQ-UHFFFAOYSA-N 0.000 description 2
- PECMDNFVBBZHDH-UHFFFAOYSA-N 2-chloro-2,2-diphenyl-1-piperidin-1-ylethanone Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C(=O)N1CCCCC1 PECMDNFVBBZHDH-UHFFFAOYSA-N 0.000 description 2
- XQYVDDAXTYTKDB-UHFFFAOYSA-N 2-chloro-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)N)C1=CC=CC=C1 XQYVDDAXTYTKDB-UHFFFAOYSA-N 0.000 description 2
- RQCVNIVJMBXZRT-UHFFFAOYSA-N 2-methylpropyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCC(C)C)C1=NC=CN1 RQCVNIVJMBXZRT-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- APKFDSVGJQXUKY-KKGHZKTASA-N Amphotericin-B Natural products O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1C=CC=CC=CC=CC=CC=CC=C[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-KKGHZKTASA-N 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 206010007134 Candida infections Diseases 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 208000007163 Dermatomycoses Diseases 0.000 description 2
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 241000223238 Trichophyton Species 0.000 description 2
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 2
- 229960003942 amphotericin b Drugs 0.000 description 2
- 201000003984 candidiasis Diseases 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 201000003929 dermatomycosis Diseases 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MCGGQYKHZGQEGN-UHFFFAOYSA-N ethyl 2-(4-chlorophenyl)-2-(1h-imidazol-2-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC(Cl)=CC=1)(C(=O)OCC)C1=NC=CN1 MCGGQYKHZGQEGN-UHFFFAOYSA-N 0.000 description 2
- DRNQRIRVMLZTTF-UHFFFAOYSA-N ethyl 2-benzyl-2-(1h-imidazol-2-yl)-3-methylbutanoate Chemical compound N=1C=CNC=1C(C(=O)OCC)(C(C)C)CC1=CC=CC=C1 DRNQRIRVMLZTTF-UHFFFAOYSA-N 0.000 description 2
- UQLDRUBJKYZDRV-UHFFFAOYSA-N ethyl 2-benzyl-2-(1h-imidazol-2-yl)-5-methylhexanoate Chemical compound N=1C=CNC=1C(CCC(C)C)(C(=O)OCC)CC1=CC=CC=C1 UQLDRUBJKYZDRV-UHFFFAOYSA-N 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 2
- 229960002867 griseofulvin Drugs 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- YCMAVBIZWABQFF-UHFFFAOYSA-N methyl 2,2-bis(4-bromophenyl)-2-(1h-imidazol-2-yl)acetate Chemical compound C=1C=C(Br)C=CC=1C(C=1C=CC(Br)=CC=1)(C(=O)OC)C1=NC=CN1 YCMAVBIZWABQFF-UHFFFAOYSA-N 0.000 description 2
- KXAQWOCSDWVABF-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2-(2-methylphenyl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C(=CC=CC=1)C)(C(=O)OC)C1=NC=CN1 KXAQWOCSDWVABF-UHFFFAOYSA-N 0.000 description 2
- RBIZUCWGJMRQKS-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2-(4-methylphenyl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC(C)=CC=1)(C(=O)OC)C1=NC=CN1 RBIZUCWGJMRQKS-UHFFFAOYSA-N 0.000 description 2
- DKQFBMYNBRIZCA-UHFFFAOYSA-N methyl 2-(2-chlorophenyl)-2-(1h-imidazol-2-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C(=CC=CC=1)Cl)(C(=O)OC)C1=NC=CN1 DKQFBMYNBRIZCA-UHFFFAOYSA-N 0.000 description 2
- ILVSUJHMWHCKOI-UHFFFAOYSA-N methyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OC)C1=CC=CC=C1 ILVSUJHMWHCKOI-UHFFFAOYSA-N 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- CJXUYNZKJHUHLE-UHFFFAOYSA-N octyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCCCCCCCC)C1=NC=CN1 CJXUYNZKJHUHLE-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- PRRHXUDAIBCCOD-UHFFFAOYSA-N propyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OCCC)C1=NC=CN1 PRRHXUDAIBCCOD-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XMAWUPHYEABFDR-UHFFFAOYSA-N 1,2-bis(4-chlorophenyl)ethane-1,2-dione Chemical group C1=CC(Cl)=CC=C1C(=O)C(=O)C1=CC=C(Cl)C=C1 XMAWUPHYEABFDR-UHFFFAOYSA-N 0.000 description 1
- ZURYEZOJWJIGHE-UHFFFAOYSA-N 2,2-bis(4-bromophenyl)acetic acid Chemical compound C=1C=C(Br)C=CC=1C(C(=O)O)C1=CC=C(Br)C=C1 ZURYEZOJWJIGHE-UHFFFAOYSA-N 0.000 description 1
- FEAODWWVYMFEKL-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid methyl 2-(1H-imidazol-2-yl)-2,2-diphenylacetate Chemical compound OC(=O)C(O)C(O)C(O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 FEAODWWVYMFEKL-UHFFFAOYSA-N 0.000 description 1
- PTKAGHMFWYFHBU-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-2,2-diphenylacetonitrile Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C#N)C1=NC=CN1 PTKAGHMFWYFHBU-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- QKLCQKPAECHXCQ-UHFFFAOYSA-N ethyl phenylglyoxylate Chemical compound CCOC(=O)C(=O)C1=CC=CC=C1 QKLCQKPAECHXCQ-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
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- MQGDDUZWULUNTO-UHFFFAOYSA-N methanesulfonic acid;methyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate Chemical compound CS(O)(=O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 MQGDDUZWULUNTO-UHFFFAOYSA-N 0.000 description 1
- WMHPZAWGENFCAS-UHFFFAOYSA-N methyl 2,2-bis(4-fluorophenyl)-2-(1h-imidazol-2-yl)acetate Chemical compound C=1C=C(F)C=CC=1C(C=1C=CC(F)=CC=1)(C(=O)OC)C1=NC=CN1 WMHPZAWGENFCAS-UHFFFAOYSA-N 0.000 description 1
- CLZGROCYYPFPAG-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-bis(4-methylphenyl)acetate Chemical compound C=1C=C(C)C=CC=1C(C=1C=CC(C)=CC=1)(C(=O)OC)C1=NC=CN1 CLZGROCYYPFPAG-UHFFFAOYSA-N 0.000 description 1
- VIOUOQGTBCDEGK-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate;naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 VIOUOQGTBCDEGK-UHFFFAOYSA-N 0.000 description 1
- AHODWVIRUBFRBH-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2,2-diphenylacetate;sulfuric acid Chemical compound OS(O)(=O)=O.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=NC=CN1 AHODWVIRUBFRBH-UHFFFAOYSA-N 0.000 description 1
- ZMSJVUYSYFSIOI-UHFFFAOYSA-N methyl 2-(1h-imidazol-2-yl)-2-methyl-3-phenylpentanoate Chemical compound N=1C=CNC=1C(C)(C(=O)OC)C(CC)C1=CC=CC=C1 ZMSJVUYSYFSIOI-UHFFFAOYSA-N 0.000 description 1
- HZXFRXXRYDAVID-UHFFFAOYSA-N methyl 2-(2-methyl-1h-imidazol-5-yl)-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)OC)C1=CN=C(C)N1 HZXFRXXRYDAVID-UHFFFAOYSA-N 0.000 description 1
- FPFJKVGMDIAFJI-UHFFFAOYSA-N methyl 2-(4-chlorophenyl)-2-(1h-imidazol-2-yl)-2-phenylacetate Chemical compound C=1C=CC=CC=1C(C=1C=CC(Cl)=CC=1)(C(=O)OC)C1=NC=CN1 FPFJKVGMDIAFJI-UHFFFAOYSA-N 0.000 description 1
- BTTBHWMYJRVGNA-UHFFFAOYSA-N methyl 2-chloro-3,3-dimethyl-2-phenylbutanoate Chemical compound COC(=O)C(Cl)(C(C)(C)C)C1=CC=CC=C1 BTTBHWMYJRVGNA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- RYQZDZLSAGLCHR-UHFFFAOYSA-N octyl 2-chloro-2,2-diphenylacetate Chemical compound C=1C=CC=CC=1C(Cl)(C(=O)OCCCCCCCC)C1=CC=CC=C1 RYQZDZLSAGLCHR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 206010034754 petechiae Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691925994 DE1925994C3 (de) | 1969-05-21 | Phenyl-imidazolyl-fettsäurederivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL80851B1 true PL80851B1 (de) | 1975-08-30 |
Family
ID=5734834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL14074470A PL80851B1 (de) | 1969-05-21 | 1970-05-20 |
Country Status (7)
| Country | Link |
|---|---|
| ES (1) | ES379870A1 (de) |
| IE (1) | IE34289B1 (de) |
| IL (1) | IL34516A (de) |
| NO (1) | NO128571B (de) |
| PH (1) | PH12184A (de) |
| PL (1) | PL80851B1 (de) |
| RO (1) | RO56292A (de) |
-
1970
- 1970-05-13 IL IL34516A patent/IL34516A/en unknown
- 1970-05-13 IE IE63070A patent/IE34289B1/xx unknown
- 1970-05-19 PH PH11460A patent/PH12184A/en unknown
- 1970-05-20 PL PL14074470A patent/PL80851B1/pl unknown
- 1970-05-20 NO NO93170A patent/NO128571B/no unknown
- 1970-05-20 RO RO6340570A patent/RO56292A/ro unknown
- 1970-05-21 ES ES379870A patent/ES379870A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL34516A0 (en) | 1970-07-19 |
| RO56292A (de) | 1974-08-01 |
| IE34289B1 (en) | 1975-04-02 |
| PH12184A (en) | 1978-11-21 |
| IE34289L (en) | 1970-11-21 |
| NO128571B (de) | 1973-12-10 |
| ES379870A1 (es) | 1972-09-16 |
| IL34516A (en) | 1973-01-30 |
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